The largest, but not the first.

The interwebs say there has been 36 municipal bankruptcy filings since January 2010, including the following eight cities and localities:
— City of Detroit
— City of San Bernardino, Calif.
— Town of Mammoth Lakes, Calf. (Dismissed)
— City of Stockton, Calif.
— Jefferson County, Ala.
— City of Harrisburg, Pa. (Dismissed)
— City of Central Falls, R.I.
— Boise County, Idaho (Dismissed)

I don’t recall the wingers laughing about Jefferson County, Alabama, deep in the heart of Mother Dixie.